Schubas Tavern ★ 4.6
$$$$
Wrigleyville / LakeviewMon 18:00-23:00, Tue-Wed 17:00-23:00, Thu 17:00-00:00, Fri 17:00-01:00, Sat 14:00-01:00, Sun 18:00-23:00.
Schubas Tavern in Chicago has run live music seven nights a week in the 1903 Schlitz tied-house on Southport since 1989, from honky-tonk to indie rock to Americana.
TipDoors usually 19:00, show at 20:00. The back room holds 165 standing; the front bar runs into the late hours after the night's show ends.
The Hideout ★ 4.7
$$$$
Wicker Park / BucktownMon varies by event, Tue-Thu 17:00-00:00, Fri-Sat 17:00-01:00, Sun varies by event.
The Hideout in Chicago is the Wabansia Avenue clapboard cottage in the Elston industrial corridor, hosting Americana, experimental and the Robbie Fulks Monday residency.
TipTuesday through Thursday close at midnight, Friday and Saturday at 01:00. The room holds about 100 and the bands play through the bar conversation.
Thalia Hall ★ 4.7
$$$$
PilsenMon-Wed varies by event, Thu-Sat 19:00 doors, varies, Sun varies by event.
Thalia Hall in Pilsen, built 1892 and modeled on the Prague State Opera House, runs touring indie, hip-hop and electronic shows in an 800-capacity balcony room.
TipDoors usually 19:00 with show at 20:00. The balcony bench seating fills first; Dusek's restaurant and Punch House bar share the building entrance.
Buddy Guy's Legends ★ 4.7
$$$$
The LoopWed-Thu 17:00-00:00, Fri-Sat 17:00-01:30, Sun 17:00-00:00. Closed Mon-Tue.
Buddy Guy's Legends in Chicago is the South Wabash blues room the man himself opened in 1989 and where he still plays a residency every January.
TipClosed Monday and Tuesday. Wednesday and Thursday close at midnight; weekends run to 01:30. Cover usually $20, kitchen serves Louisiana barbecue.
Cindy's at Chicago Athletic Association ★ 4.5
$$$$
$22 cocktails, reservations via OpenTableThe LoopMon-Thu 11:00-23:00, Fri 11:00-00:00, Sat 10:00-00:00, Sun 10:00-23:00.
Cindy's rooftop in Chicago sits on the 13th floor of the Chicago Athletic Association with all-season terrace seating that frames Millennium Park and Lake Michigan.
TipWeekends fill from 21:00; reserve via OpenTable or arrive at 16:00 for the sunset window. The terrace stays heated and open year-round.
LH Rooftop ★ 4.4
$$$$
$20 cocktails, OpenTable reservationsThe LoopDaily 11:00-00:00.
LH Rooftop in Chicago crowns LondonHouse on the corner of Wacker and Michigan with three tiers of terrace facing the river and the Trump Tower clock face.
TipOpen every day until midnight, food last call 22:00. The top tier is the photo spot; weekend brunch from 11:00 is the easy walk-in window.